diff --git a/features/deploy.feature b/features/deploy.feature
index 36e29051..5f585fec 100644
--- a/features/deploy.feature
+++ b/features/deploy.feature
@@ -52,3 +52,12 @@ Feature: Deploy
     When I run cap "deploy:symlink:release"
     Then the current directory will be a symlink to the release
 
+  Scenario: Rolling Back
+    Given I make 2 deployments
+    When I run cap "deploy:rollback"
+    Then the current symlink points to the previous release
+
+  Scenario: Rolling Back to a specific release
+    Given I make 3 deployments
+    When I rollback to a specific release
+    Then the current symlink points to that specific release
diff --git a/features/step_definitions/assertions.rb b/features/step_definitions/assertions.rb
index 6926407c..0ff483af 100644
--- a/features/step_definitions/assertions.rb
+++ b/features/step_definitions/assertions.rb
@@ -6,7 +6,9 @@ end
 
 Then(/^git wrapper permissions are 0700$/) do
   permissions_test = %Q([ $(stat -c "%a" #{TestApp.git_wrapper_path.shellescape}) == "700" ])
-  expect(vagrant_cli_command("ssh -c #{permissions_test.shellescape}")).to be_success
+  _stdout, _stderr, status = vagrant_cli_command("ssh -c #{permissions_test.shellescape}")
+
+  expect(status).to be_success
 end
 
 Then(/^the shared path is created$/) do
@@ -124,3 +126,15 @@ end
 Then(/doesn't contain "([^"]*)" in the output/) do |expected|
   expect(@output).not_to include(expected)
 end
+
+Then(/the current symlink points to the previous release/) do
+  previous_release_path = @release_paths[-2]
+
+  run_vagrant_command(symlinked?(TestApp.current_path, previous_release_path))
+end
+
+Then(/^the current symlink points to that specific release$/) do
+  specific_release_path = TestApp.releases_path.join(@rollback_release)
+
+  run_vagrant_command(symlinked?(TestApp.current_path, specific_release_path))
+end
diff --git a/features/step_definitions/cap_commands.rb b/features/step_definitions/cap_commands.rb
index c72d9f4a..57b0000d 100644
--- a/features/step_definitions/cap_commands.rb
+++ b/features/step_definitions/cap_commands.rb
@@ -13,3 +13,9 @@ end
 When(/^I run "(.*?)"$/) do |command|
   @success, @output = TestApp.run(command)
 end
+
+When(/^I rollback to a specific release$/) do
+  @rollback_release = @release_paths.first.split("/").last
+
+  step %Q{I run cap "deploy:rollback ROLLBACK_RELEASE=#{@rollback_release}"}
+end
diff --git a/features/step_definitions/setup.rb b/features/step_definitions/setup.rb
index 69b2b9a6..dcf21dc7 100644
--- a/features/step_definitions/setup.rb
+++ b/features/step_definitions/setup.rb
@@ -21,10 +21,16 @@ end
 
 Given(/^file "(.*?)" exists in shared path$/) do |file|
   file_shared_path = TestApp.shared_path.join(file)
-  run_vagrant_command("mkdir -p #{TestApp.shared_path}")
+  run_vagrant_command("mkdir -p #{file_shared_path.dirname}")
   run_vagrant_command("touch #{file_shared_path}")
 end
 
+Given(/^all linked files exists in shared path$/) do
+  TestApp.linked_files.each do |linked_file|
+    step %Q{file "#{linked_file}" exists in shared path}
+  end
+end
+
 Given(/^file "(.*?)" does not exist in shared path$/) do |file|
   file_shared_path = TestApp.shared_path.join(file)
   run_vagrant_command("mkdir -p #{TestApp.shared_path}")
@@ -60,3 +66,14 @@ end
 Given(/^a stage file named (.+)$/) do |filename|
   TestApp.write_local_stage_file(filename)
 end
+
+Given(/^I make (\d+) deployments$/) do |count|
+  step "all linked files exists in shared path"
+
+  @release_paths = (1..count.to_i).map do
+    TestApp.cap("deploy")
+    stdout, _stderr = run_vagrant_command("readlink #{TestApp.current_path}")
+
+    stdout.strip
+  end
+end
diff --git a/features/support/remote_command_helpers.rb b/features/support/remote_command_helpers.rb
index 91420c1f..784dd2c8 100644
--- a/features/support/remote_command_helpers.rb
+++ b/features/support/remote_command_helpers.rb
@@ -15,6 +15,10 @@ module RemoteCommandHelpers
     %Q{[ -#{type} "#{path}" ]}
   end
 
+  def symlinked?(symlink_path, target_path)
+    "[ #{symlink_path} -ef #{target_path} ]"
+  end
+
   def safely_remove_file(_path)
     run_vagrant_command("rm #{test_file}")
   rescue
diff --git a/features/support/vagrant_helpers.rb b/features/support/vagrant_helpers.rb
index 1dbdf874..a0465a2a 100644
--- a/features/support/vagrant_helpers.rb
+++ b/features/support/vagrant_helpers.rb
@@ -1,4 +1,4 @@
-require "English"
+require "open3"
 
 module VagrantHelpers
   extend self
@@ -16,17 +16,18 @@ module VagrantHelpers
 
   def vagrant_cli_command(command)
     puts "[vagrant] #{command}"
-    Dir.chdir(VAGRANT_ROOT) do
-      `#{VAGRANT_BIN} #{command} 2>&1`.split("\n").each do |line|
-        puts "[vagrant] #{line}"
-      end
+    stdout, stderr, status = Dir.chdir(VAGRANT_ROOT) do
+      Open3.capture3("#{VAGRANT_BIN} #{command}")
     end
-    $CHILD_STATUS
+
+    (stdout + stderr).each_line { |line| puts "[vagrant] #{line}" }
+
+    [stdout, stderr, status]
   end
 
   def run_vagrant_command(command)
-    status = vagrant_cli_command("ssh -c #{command.inspect}")
-    return true if status.success?
+    stdout, stderr, status = vagrant_cli_command("ssh -c #{command.inspect}")
+    return [stdout, stderr] if status.success?
     raise VagrantSSHCommandError, status
   end
 end